Comparison of the antioxidant activity of Echium amoenum Fisch and C.A. Mey, Chamaemelum nobile (L.) All and Camellia sinensis (L.) O. Kuntze on oleic acid photooxidation using water soluble porphyrin complexes as catalyst

Document Type : Research Article


1 1Assistant Professor of Inorganic chemistry and Nanochemistry Department, Faculty of Chemistry, Kharazmi University, Tehran, Iran

2 MSc Graduated of Inorganic chemistry and Nanochemistry Department, Faculty of Chemistry, Kharazmi University, Tehran, Iran


Lipid photooxidation is the undesirable chemical process in which singlet oxygen result in the peroxidation of fatty acids. In this study leaves aqueous extract of Camellia sinensis (L.) O. Kuntze and flower extracts of Chamaemelum nobile (L.) All and Echium amoenum Fisch and C.A. Mey collected from natural habitats in Lahijan, Shiraz and Golestan National Park, respectively. Aqueous extracts were extracted using maceration method. Generation of singlet oxygen and peroxide products in the presence of H2TCPP (meso-tetra-carboxy phenyl porphyrin) were proved by 1H NMR spectroscopy, UV-Vis spectroscopy and iodometric titration method. Aqueous extract of Echium amoenum Fisch and C.A. Mey flowers, aqueous extract of Camellia sinensis (L.) O. Kuntze leaves, aqueous extract of Chamaemelum nobile (L.) flowers and Ascorbic acid as a chemical antioxidant indicated an inhibition of 42.75%, 38.34%, 36.98%, 33.51% and 20.32% on peroxidation of oleic acid, respectively. The results of this study also showed that the antioxidant activity of Echium amoenum Fisch and C.A. Mey in organic solvents such as acetonitrile, ethanol and methanol solvents are maintained.


Main Subjects

[1] Wang, S.Y., Jiao, H. (2000). Scavenging Capacity of Berry Crops on Superoxide Radicals, Hydrogen Peroxide, Hydroxyl Radicals and Singlet Oxygen. J. Agric. Food Chem., 48, 5677−5684.
[2] Schumacker, P.T. (2015). Reactive Oxygen Species in A Dance with the Devil. Cancer Cell., 27, 156-157.
[3] Andrade-Cuvi, M.J., Moreno, Carlota., Zaro, M.J., Vicente, A.R., Concellón, A. (2017). Improvement of the Antioxidant Properties and Postharvest Life of Three Exotic Andean Fruits by UV-C Treatment. J. Food Qual., 2017, 1-10.
[4] Berneburg, M., Plettenberg, H., Medve-Konig, K., Pfahlberg, A., Gers-Barlag, H., Gefeller O., Krutmann, J. (2004). Induction of the photoaging-associated mitochondrial common deletion in vivo in normal human skin. J. Invest. Dermatol., 122, 1277–1283.
[5] Hanson, K.M., Simon, J.D. (1998). Epidermal trans-urocanic acid and the UV-A-induced photoaging of the skin. Proc. Natl. Acad. Sci. U.S.A., 95, 10576–10578.
[6] Devary, Y., Gottlieb, R.A., Smeal, T., Karin, M. (1992). The mammalian ultraviolet response is triggered by activation of src tyrosine kinases. Cell., 71, 1031–1091.
[7] Min, D.B., Boff, J.M. (2002). Chemistry and Reaction of Singlet Oxygen in Foods. Compr Rev Food Sci Food Saf., 1, 58-61.
[8] Choe, E.,  Min, D.B. (2006).  Mechanisms and Factors for Edible Oil Oxidation. Compr Rev Food Sci Food Saf ., 5, 169 – 186.
[9] Gęgotek, L.A., ybałtowska-Kawałko, P.R., Skrzydlewska, E. (2017). Rutin as a Mediator of Lipid Metabolism and Cellular Signaling Pathways Interactions in Fibroblasts Altered by UVA and UVB Radiation. Oxid Med Cell Longev., 2017, 1-21.
[10] Dobarganes, M.C., Velasco, J. (2002). Analysis of lipid hydroperoxides. Eur J Lipid Sci Technol., 104, 420-428.
[11] DeRosa, M., Crutchley, R. (2002). Photosensitized singlet oxygen and its applications. Coord. Chem. Rev., 233, 351-371.
[12] Huda- Faujan, N., Noriham, A., Norrakiah, A., Babji, A. (2009). Antioxidant activity of plants methanolic extracts containing phenolic compounds. Afr J Biotechnol., 8, 484- 489.
[13] Abebe., W. (2002). Herbal medication: potential for adverse interactions with analgesic drugs. J Clin Pharm Ther., 27, 391-401.
[14] O’Hara, M., Kiefer, D., Farrell, K., Kemper, K.A. (1998). A review of 12 commonly used medicinal herbs. Arch Fam Med., 7, 523–536.
[15] Kobayashi, Y., Nakano, Y., Sakai, A., Kamiya, K.T. (2003). Dietary intake of the flower extracts of German chamomile (Matricariarecutita L) inhibited compound 48/80-induced itch-scratch responses in mice. Phytomedicine., 10, 657-64.
[16] Knor, F.J., Vellosa, J.C.R., Beltrame, F.L., Pereira, V.P. (2014). Determination of phenolic compounds and antioxidant activity of green, black and white teas of Camellia sinensis (L.) Kuntze. Theaceae. Rev. Bras. Plantas Med., 16, 490-498.
[17] Sharifzadeh, A., Jebeli Javan, A., Shokri, H., Abbaszadeh, S., Keykhosravy, K. (2016). Evaluation of antioxidant and antifungal properties of the traditional plants against foodborne fungal pathogens. J Mycol Med., 26, 11-17.
[18] Abed, A., Vaseghi, G., Jafari, E., Fattahian, E., Babhadiashar, N., Abed, M. (2014). Echium Amoenum Fisch. Et Mey: A Review on its Pharmacological and Medicinal Properties. Asian J. Med. Pharm. Res., 4, 21-23.
[19] Ghahraman, A. (1978). The Flora of Iran. National Society of Natural Resources Protection., Tehran, Volume 1, pp 74 - 75.
[20] Heidari, M.R., Mandegary, A., Hosseini, A., Vahedian, M. (2006). Anticonvulsant Effect of Methanolic Extract of Echiumamoenum Fisch and C.A. Mey. Against Seizure Induced by Picrotoxin in Mice. PJBS., 9, 772-776.
[21] Terao, J., Minami, Y., Bando, N. (2011). Singlet molecular oxygen-quenching activity of carotenoids: relevance to protection of the skin from photoaging. J Clin Biochem Nutr., 48, 57-62.
[22] Kim, S.H., Lee, L.S., Bae, S.M., Han, S.J., Lee B.R., Ahn, W.S. (2008). Antimicrobial and antifungal effects of a green tea extract against vaginal pathogens. J Womens Health Gend Based Med., 1, 27-28.
[23] Lindsey, J.S., Wagner, R.W. (1989). Investigation of the Synthesis of Ortho-Substituted Tetraphenylporphyrins. JOC., 54, 828–836.
[24] Hajimohammadi, M., Safari, N., Mofakham, H., Deyhimi, F. (2011). Highly selective, economical and efficient oxidation of alcohols to aldehydes and ketones by air and sunlight or visible light in the presence of porphyrin sensitizers. Green Chem., 13, 991-997.
[25] Barthel, G., Grosch, W. (1974). Peroxide value determination-Comparison of some methods. J. Am. Oil Chem. Soc., 51, 540-544.
[26] Bonnett, R., Martinez, G. (2001). Photobleaching of sensitisers used in photodynamic therapy. Tetrahedron Lett., 57, 9513.
[27] Chen, Y., Xu, S., Li, L., Zhang, M.J. Shen, T. (2001). Active oxygen generation and photo-oxygenation involving temporfin (m-THPC). Dyes Pigm., 51, 63-69.
[28] Nor, F.M., Mohamed, S., Idris, N.A., Mail, R. (2008). Antioxidative properties of curcumaga leaf extract in accelerated oxidation and deep frying studies. J Am Oil Chem Soc., 86, 141-147.
[29] Che Man, Y.B., Jaswir, I. (2000). Effect of rosemary and sage extracts on frying performance of  refined, bleached and deodorized  (RBD) palm olein during deep-fat frying. Food Chem., 69, 301–307.
[30] Naz, S., Siddigi, R., Sheikh, H., Saeed, SA. (2005). Deterioration of olive, corn and soybean oils due to air, light, heat and deep frying.  Food Res Intern., 38, 127-134.
[31] Pérez-Jiménez, J., Neveu, V., Vos, F., Scalbert, A. (2010). Identification of the 100 richest dietary sources of polyphenols: an application of the Phenol-Explorer database.  Eur J Clin Nutr., 64, 112–120.
[32] Carnat, A., Carnat, A.P., Fraisse, D., Ricoux, L., Lamaison, J.L. (2004). The aromatic and polyphenolic composition of Roman camomile tea. Fitoterapia., 75, 32-38.
[33] Chaouche, T.M., Haddouchi, Farah., Ksouri, R., Atik-Bekkara, F. (2014). Evaluation of antioxidant activity of hydromethanolic extracts of some medicinal species from South Algeria. JCMA., 77, 302-307.